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[ CAS No. 392-83-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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2D 3D

Chemical Structure| 392-83-6

Chemical Structure| 392-83-6

Structure of 392-83-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 392-83-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 392-83-6 ]

SDS Specification

Alternatived Products of [ 392-83-6 ]

Product Citations

Product Details of [ 392-83-6 ]

CAS No. :	392-83-6	MDL No. :	MFCD00000373
Formula :	C₇H₄BrF₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	RWXUNIMBRXGNEP-UHFFFAOYSA-N
M.W :	225.00	Pubchem ID :	9806
Synonyms :

Calculated chemistry of [ 392-83-6 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.14
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.17
Log Po/w (XLOGP3) :	3.78
Log Po/w (WLOGP) :	4.62
Log Po/w (MLOGP) :	4.1
Log Po/w (SILICOS-IT) :	3.51
Consensus Log Po/w :	3.63

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.95
Solubility :	0.025 mg/ml ; 0.000111 mol/l
Class :	Soluble
Log S (Ali) :	-3.47
Solubility :	0.0756 mg/ml ; 0.000336 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.14
Solubility :	0.0162 mg/ml ; 0.0000719 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.16

Safety of [ 392-83-6 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 392-83-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 392-83-6 ]
Downstream synthetic route of [ 392-83-6 ]

[ 392-83-6 ] Synthesis Path-Upstream 1~2

1
[ 392-83-6 ]
[ 87199-17-5 ]
[ 198205-95-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium carbonate In 1,4-dioxane; water at 80 - 100℃;	To a stirred solution of 2-trifluromethyl-bromobenzene (0.7 g, 2.75 mmol) and 4-carbaldehyde boronic acid (0.5 g, 3.3 mmol) in dioxane (20 ml_) under nitrogen at 80 ⁵C was added Pd(PPh₃)₄ (0.05 g) followed by the addition of a solution of Na₂CO₃ (0.7 g) in H₂O (5 m). The mixture was stirred at 100 ⁵C for 6 h. The solvent was evaporated and the residue was diluted to 50 ml with EtOAc and washed with H₂O. The solvent was devaporated to dryness and the residue was purified by FCC (SiO₂) to give the title compound (0.61 g; 88percent), as creamy solid. ¹H-NMR (CDCI₃) 7.49 (d, 1 H, J = 7.41 Hz); 7.48 (d, 2H, J = 8.13 Hz); 7.61 - 7.53 (m, 2H); 7.76 (d, 1 H, J = 7.8 Hz); 7.91 (d, 2H, J = 8.34 Hz); 10.07 (s, 1 H).

Reference： [1] Patent: WO2010/42998, 2010, A1, . Location in patent: Page/Page column 95

2
[ 392-83-6 ]
[ 104-88-1 ]
[ 198205-95-7 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 17, p. 4606 - 4609

[ 392-83-6 ] Synthesis Path-Downstream 1~6

1
[ 392-83-6 ]
[ 75-07-0 ]
[ 79756-81-3 ]

Reference： [1]Journal of Chemical Research, Miniprint,1981,p. 3216 - 3245
[2]Polymer,2011,vol. 52,p. 949 - 953

2
[ 124-38-9 ]
[ 392-83-6 ]
[ 177420-64-3 ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 2767 - 2770

3
aqueous ammonium chloride [ No CAS ]
n-butyllithium hexane [ No CAS ]
[ 426219-35-4 ]
[ 392-83-6 ]
[ 426219-43-4 ]
[ 426219-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran;	Example 10 Production of 6-(7-hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methyl-2-naphthamide Under an argon atmosphere, 2-bromobenzotrifluoride (33.05 g) was dissolved in dry THF (600 ml), and the mixture was cooled to -65 C. in a dry ice-acetone bath. An n-butyl lithium hexane solution (1.6M: 93.7 ml) was added with stirring and the mixture was stirred at the same temperature for 30 min. After stirring the mixture, a dry THF (2.88L) solution of <strong>[426219-35-4]6-bromo-N-methyl-2-naphthamide</strong> (38.03 g) cooled to 10 C. was added at not more than -55 C. The mixture was stirred for 20 min. An n-butyl lithium hexane solution (1.6M: 94.5 ml) was added at not more than -65 C. The mixture was stirred for 30 min and 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (14.66 g) in a dry THF solution (240 ml) was added dropwise. The mixture was stirred at the same temperature for 1.5 h and saturated aqueous ammonium chloride solution (520 ml) was added to stop the reaction. The solvent was evaporated under reduced pressure and an ethanol-soluble material was extracted from the resulting residue and the solvent was evaporated again. The resulting residue was purified by flash silica gel column chromatography (eluent; chloroform/methanol containing ammonia (7%); 19/1?9/1). The elude was recrystallized from methanol to give the title compound (16.44 g) as colorless crystals. The physical and chemical data were identical with those of the compound obtained in Example 5.

Reference： [1]Patent: US2004/33935,2004,A1

4
[ 1455-20-5 ]
[ 392-83-6 ]
[ 1044231-42-6 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 425 - 432
[2]Chemistry - A European Journal,2011,vol. 17,p. 6453 - 6461
[3]Advanced Synthesis and Catalysis,2007,vol. 349,p. 2507 - 2516

5
[ 820971-67-3 ]
[ 392-83-6 ]
[ 1241898-68-9 ]

Yield	Reaction Conditions	Operation in experiment
		ter /-Butyl 3 - r2-(trifluoromethyl)benzoyll azetidine- 1 -carboxylate; To a solution of 1 -bromo-2-(trifluoromethyl)benzene (1.01 g, 4.5 mmol) and TMEDA (1.36 mL, 9.0 mmol) in THF (20 niL) at -78 0C was added slowly a solution of tenbutyl lithium (1.7 M in hexanes, 5.3 mL, 9.0 mmol). After stirring at -78 0C for 0.5 h, a solution of the product of tert-butyl 3-[methoxy(methyl)amino]carbonyl}azetidine-l -carboxylate (1.0 g, 4.1 mmol) in THF (5 mL) was added via syringe and the reaction mixture was allowed to warm to room temperature. After 6 h, the reaction was quenched by the addition of saturated aqueous NH4Cl solution (5 mL). The mixture was poured into a 250 mL separatory funnel containing saturated aqueous NH4Cl solution (100 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography through silica gel, eluting with 5% EtOAc in hexanes to 25% EtOAc in hexanes as a gradient, afforded the title compound.
		Step 2: tert-Butyl 3-[2-(trifluoromethyl)benzoyl]azetidine-1-carboxylate To a solution of 1-bromo-2-(trifluoromethyl)benzene (1.01 g, 4.5 mmol) and TMEDA (1.36 mL, 9.0 mmol) in THF (20 mL) at -78 C. was added slowly a solution of tert-butyl lithium (1.7 M in hexanes, 5.3 mL, 9.0 mmol). After stirring at -78 C. for 0.5 h, a solution of the product of <strong>[820971-67-3]tert-butyl 3-[methoxy(methyl)amino]carbonyl}azetidine-1-carboxylate</strong> (1.0 g, 4.1 mmol) in THF (5 mL) was added via syringe and the reaction mixture was allowed to warm to room temperature. After 6 h, the reaction was quenched by the addition of saturated aqueous NH4Cl solution (5 mL). The mixture was poured into a 250 mL separatory funnel containing saturated aqueous NH4Cl solution (100 mL) and extracted with EtOAc (3*50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by column chromatography through silica gel, eluting with 5% EtOAc in hexanes to 25% EtOAc in hexanes as a gradient, afforded the title compound.

Reference： [1]Patent: WO2010/94126,2010,A1 .Location in patent: Page/Page column 116
[2]Patent: US2011/301143,2011,A1 .Location in patent: Page/Page column 67

6
[ 41014-43-1 ]
[ 762-04-9 ]
[ 392-83-6 ]
[ 1337540-39-2 ]

Reference： [1]Polyhedron,2011,vol. 30,p. 2746 - 2757

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Alkylbenzene ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Vilsmeier-Haack Reaction

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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
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P270	Do not eat, drink or smoke when using this product.
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Code	Phrase
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